A few weeks ago, I booked a customized tour of Iceland with Noken, and I did it in about five minutes. All I had to do was to tell Noken how long I planned to go, what level of hotel and car I wanted, and then I had the option to add on a few extras, and within minutes my entire trip was booked. I had a connection to my own personal trip concierge and a custom app that outlined my trip. I literally haven't had to think about it since I booked it--no worries about reservations, what to do when, or doing additional research, things I really don't have the time for.

Some people really like researching travel--and you can spend weeks and weeks doing it. There is more information on the web, not to mention all the friend recs you can get, than anyone with a full time job can really handle. For the rest of us that don't have time, and just want to know that someone who does nothing but think about this all the time took care of all this for us--and that our plans, tickets, maps, etc. are all in one place on our phones, Noken us for us.

When I was growing up, we took a few road trips to see my brother in Chicago and then down to Florida, but we weren't international travelers. My impression of international travel came from Mario Perillo, TV's "Mr. Italy" who used to advertise his family's tour business on NY television all the time...

My grandparents went on one of those tours in the early 80's. They rode a bus with a bunch of other senior citizens and undoubtedly followed around some guy with an umbrella or flag or something. That's not something I had any interest in.

Travel changed a lot over the next few years. The internet provided a firehose of reviews, lists, and research, which was nice for a while, but then it became overwhelming. In a world of unlimited choices, curation, transparancy and simplicity became more valuable.

We went from searching millions of recipes to subscribing to meals that someone else picks for us.

We went from comparing every last product out there to trusting single product companies whose value proposition was straightforward and whose customer service was great--whether it was for buying mattresses, sheets, luggage, etc.

Marc Espana and Emily Brockway, the Co-founders of Noken asked why booking travel couldn't be as simple as buying the luggage for your trip. Instead of sifting through endless sources of information, why couldn't a company just say "Here, we did this for you".

They built the answer, and all you have to do is hear from the customers to find out the results:

They didn't just set out to make travel easier because it's a big opportunity with nothing else like it out there--they did it to build cross-cultural empathy at a time when that is in short supply. The events of the last year affected this team personally--being LGBTQ and female founders, as well as having a Dreamer on the team. It's been shown that the more you travel, the less you think of people who are different than you as your enemy or someone to fear. One of the best way to make someone more empathetic is to hand them a passport and show them the world and its people.

The tours are an order of magnitude less expensive because the company doesn't have to pay for infrastructure on the ground--it's all in your custom app. On top of that, unlike almost everything else in the travel space, they're not offering yet another search based route to a commodity product. They've created something branded that a consumer can be loyal to and come back again and again as new countries are added (they have Iceland and Columbia currently). The trips are Instagram-worthy, creating viral loops that you simply don't see with the Kayaks of the world. This addresses some of the acquisition economics that scare some investors away from the travel space, because no one wants to invest in a business competing for the same customer as everyone else with a completely undifferentiated product.

I backed Noken's pre-seed round back in August. The funny story about that is that they weren't really raising, but just looking to build connections for their seed. At the time, I was looking for a company to present to an investor education group that I run to help teach people about how VC meetings work. When Emily wrote me, I responded by accepting the meeting request, but letting her know that it wasn't just going to be with me--but that she and Marc would be sharing their company like patients in an operating theater, with 30 people in the round listening in on the conversation. Unfazed, they gave a great presentation and shared how they had done over $100k in revenue, without even having a real app. It turned out they had been using Invision demo apps the whole time for their customers to use in their trips--and yet still getting rave reviews with only a fraction of the functionality.

I talked them into taking money from me head of a real round and they've been amazing to work with over the past seven months or so. I'm excited about their ability to build a seriously large consumer brand in this category in a way that doesn't currently exist.

When said to a VC, this is one of the biggest BS lines out there. You're literally talking to an investor, and if they offered you a big check at a great deal, you'd take it, no? So, how could you say you aren't fundraising?

On the other hand, some founders *literally* aren't fundraising. They won't share any info on what's going on with their company, even with investors that are really excited about their concept.

Is this a missed opportunity or just insurance that they're going to put their best foot forward in an organized process? After all, they have a company to run now and success at meeting your current goals is going to improve your chances of a successful fundraise later, right?

Well, it all depends, right?

Actually, I tend to lean more on the relationship building side, for a couple of reasons.

First, in the early stages, there's a lot more information that can be gleaned about you than we can know for sure about the success of your company. How you think, what your plans are, etc. are all keys to helping VCs figure out whether they want to back you--and before a Series A, you really don't *know* for sure whether something is going to be a success, no matter how much data you have.

That's why the first check for a Series A firm is so small relative to the size of their fund. Think about it... if a $350 million dollar fund leads an $8mm round, they're probably doing about $6.5 million of it. That's less than 2% of their fund, and of all of their checks were like that, they'd be doing 55 deals in a fund, or over 2x what you actually statistically need for diversification. You think you're getting this big fat check compared to the seed money you raised, but they're actually doing something more like dipping their toes in the water. It's less signal than you think.

They know there's not a lot of data yet and it's still more of a flyer, which is why I think putting your head down to optimize your company to 110% to try to get your next round isn't the right strategy--because it's not the mindset the investors are in. It's a game you're the only one playing. Not only that, it's a game that you'll never be more poorly equipped to play. Company success is a function of resources--people and money, neither of which you have much of.

It's showing up to a gun fight with a Pez dispenser.

Given that so much of the bet at these early stages, even at the Series A comes down more to "Do I believe what this founder believes?" it strikes me that actually talking to an investor, sharing your vision, and actually starting to work together feels like a better strategy than going silent until "Pitch Day" when you show up all ready and prepared, expecting term sheets in just a couple of weeks.

This is especially the case with a strong founder who has the best company in a space--because getting to know more investors wards off VCs from investing in your competitors. You'll clearly come off so much better than them that no one is going to want to settle for second fiddle. They'd just as soon go find another space where they can find the category leader.

A lot of founders worry about information sharing. The fact of the matter is that you're not the only one who has thought about this idea--and you'd have to be pretty egotistical to imagine you had. What you should imagine is that you're the best team to execute on it--so that no matter what you tell an investor, it won't matter who knows what, because just knowing the plan doesn't mean executing on it.

One thing going on behind the scenes that founders might not be conscious of is intra-firm dynamics. One partner might want to meet with you while you're "not raising" in order to build the case inside their firm for doing this deal. Maybe not everyone in the partnership is there on "Casper for Congressional Testimony Seat Cushions", so they're meeting with you to socialize the idea of the company ahead of you actually being ready for a check. Keeping close to the vest in this scenario would make it impossible to get the partnership to a yes if you just showed up after running silent.

Here's something else to consider--the getting to know you phase has very different expectations than the due diligence phase. If your company is a work in progress and you didn't show up to "pitch" then an investor is absolutely going to understand if you don't have the perfect deck or all the customer acquisition data figured out yet. Founders worried about this need to stop acting as if investors have never seen a startup before.

Too often, because most investor conversations result in a no, founders start telling themselves all sorts of reasons what caused that result. Thinking you were underprepared to discuss your company and that more model tinkering and deck stylizing is just bad thinking. Investors have seen a wide variety of companies before at various levels of rough edges. They can recognize a deal they want to be in versus not.

Besides, would you rather get a "no" after knowing that the investor absolutely understood what you were trying to do and you had enough time to share why you were excited, or would you rather walk out feeling like the pitch process was very rushed, and you didn't get everything out there in the shortened cycle you actually had to do the pitch?

On top of all this, what about your own due diligence as a founder? Don't you want to get to know different investors over time to decide who you want to be working with? It's like making a hire that you can't fire--so having the chance for multiple interviews over a longer period of time is important and to your advantage.

My advice is to work with your current investors, if you have any, to pick out a short list--maybe three or four investors--and gauge their interest. See whose eyes light up when you tell them about the company or who gives you a reason why they've been looking at that space. Have an introductory meeting, and if you feel like you would like working with them, get their feedback on what's going to be important and what should be a priority when. Do some deeper dive working sessions that give that investor some insight into what it would be like to work with you. Get them to do some homework for you, too--especially around hiring. See what kind of candidates they send your way, or what kind of partner introductions they can make.

Be cautious about your time, of course--cutting off these conversations if you know this is an investor you're not excited about or you're pretty sure they're not excited about you.

I am convinced, however, that investors come on more because they believe your vision and trust you, conclusions that can only be reached over time through experience, than because you achieved some operational milestone.

It's really hard to advise a company when you don't have all the information--and no one has more information than the CEO of the company. Sometimes, you might believe the CEO is ill-informed, and you're a check on the amount of homework they've done to seek out solutions to a problem, or which metrics or signals they're paying close enough attention to. That's a really useful function for any kind of advisor, be it a board member, investor, or someone advising about a specific aspect of the company.

However, it's very tempting as an investor to get into the habit of telling the founder what you think about all sorts of things, before you've asked them for what they would propose as the way forward, or when you haven't even agreed on what's a problem.

Following this strategy as the CEO means that you're taking the advice of someone who, at best, has 1 out of 30 days of experience with the company via a monthly board meeting, and two, might be pattern matching for a bunch of other companies that isn't the company at hand.

Lots of different companies operate in lots of different ways--and they've done so across a lot of different environments. If you started a tech company 25 years ago, you did so before the internet was really a thing for everyone. If you started one 20 years ago, you did so before broadband was really a thing for everyone. It was just 15 years ago that no one had smart phones. It was merely 10 years ago that Facebook hadn't even cracked a billion dollars of ad revenue (It did nearly $40B last year).

So, even when you're talking to smart people who already built their businesses, they did so in very different environments, with different teams than what you have now.

As the CEO, you should be prepared to make decisions that you stand by and not have to go to advisors and investors with every issue. We're here to audit your thinking, not to do it for you.

Here's a good way to do that:

1) Have a way to organize the company's priorities over time and measure results.

Start with your long term goals, this year's goals, this quarter's goals, etc. Drill that down to goals for various teams. This is what's known as Objectives and Key Results. It's never to early to start using them. This way, everyone around the table, including investors, management, and employees can see the plans laid out, and have something to weigh in on.

This way, we can all be standing on common ground and we have an objective way to discuss what's working and what's not.

Processes always trump "gut" when you have the time.

2) Do your homework.

If something seems not right, and you don't know why, you should sit down and talk to a few smart people who've probably been through something like this before--and if you don't know anyone, definitely ask investors.

You're much better off asking investors for resources to do your own research than just asking what the investor thinks. If nothing else, it helps you build up a network of other founders and executives that you can count on whose experience dwarfs what the handful of your active investors have.

3) Present your observations, findings and proposed solutions.

It's not a useful exercise to just pronounce tactics at a board meeting without context, and certainly not to blindly follow advice because you heard it was something you should do.

What I find most useful is that you give us the opportunity to understand why you thought something was a) important and b) in need of change or improvement. Hopefully, it traces back to your stated objectives--in which case, it's something we all agreed on prior.

It also allows for an investor to see why you're focused on something and help you with prioritization--because maybe it's not something that actually needs to be addressed right now given your limited resources.

I want to hear what the CEO thinks first--before I respond to a question. If nothing else, how else is a CEO supposed to learn the responsibility of setting direction and making good decisions? It's too easy to just ask others for their opinions if you aren't required to make your case for something first.

At the end of the day, there are going to be hundreds of decisions I'm not around for as a board member, observer, advisor, etc., and the best thing I can do for a company is help the CEO create a process that makes them the best decision maker possible.

Recently, Brooklyn City Councilman Rafael Espinal proposed a bill last Thursday that aims to make it illegal for private employees in New York City to be required to check and respond to their work emails or take part in work-related electronic communications during non-work hours. The idea is great--I'm sure everyone would love to live in a world where the moment we walk out of the office, the world just stops, and waits for us to return the next day.

That's just not realistic at all. Just ask his campaign staff. Did he ever send an e-mail to them "off hours"?

Hard to see how he'd win without doing so.

Don't get me wrong--work/life balance is really really important. Firms recognize this. They're doing more and more to facilitate healthy approaches to work, offering meditation classes, paying for gym memberships, creating paths for parents returning to the workplace to work flexible schedules, etc.

Creating legislation around this creates move problems than it solves. Plenty of perfectly healthy work environments occasionally dip into "off hours" time. Maybe I've decided to work late because I took the day off tomorrow, but I need some bit of information from a colleague. Maybe that person is difficult to work with generally, and is on the verge of getting fired. A nice colleague might respond to my "Hey, what revenues were you projecting this year?" text with a quick response, but this person just ignores it. Now I can't do my job because he doesn't feel like doing his.

After generally mistreating other employees, when they finally fire him, now he uses this law as his cover--and the company is potentially going to get fined.

White collar workers connected by e-mail are quite capable of maintaining the proper balance here through clear communication of expectations. This is why work hours aren't defined--because if I say 9-5, the person who likes working 10-6 is going to be less productive. When you create a rule for everything, you lose efficiency. When do work hours end? 5? 6? 7? What about the day before a big client presentation? What about when your co-workers are doing a presentation in SF and it's 7:30PM here? They're working, but you're "off?" They need the latest copy of the deck and they're trying to reach you, but you just sit there with your arms crossed because you're "off the clock?" Is a sales pitch an "emergency?"

Good luck enforcing this.

Trying to litigate what constitutes an "emergency" e-mail is foolhardy and isn't worth the government's time, not to mention that these mobile technologies actually allow people to be better at work life balance in many cases. Do you need to be checking e-mail 24/7? No. Would it be helpful to respond to something after you've put the kids to bed, so that your earlybird co-worker has what they need on their 6am train ride into the city? Yeah. And if you're on your phone tweeting cat pictures, your co-worker has every right to get annoyed that you couldn't get them a quick answer on that memo if they're paying you over $100k/year.

If you really want to go after abuse of workers, check out all the delivery employees who bring your lunch by bike without Worker's Comp insurance and without any Fair Work Week protections, because they're all 1099 employees.

Given that he doesn't have much to do these days, Barack Obama goes poking around Crunchbase one day and he stumbles upon your startup. He finds your company, and obviously being super impressed, he reaches out and asks you what he can do to help.

What do you ask of him? (Or anyone else on that level...)

This isn't an easy answer. The truth is, you're probably not ready to handle whatever the former leader of the free world can do for you, but you're obviously not going to let this opportunity go, right? You have to come up with something.

This is a problem of multiple dimensions:

First off, you have to narrow the scope of possibilities. This is hard. Obama could probably do just about *anything* for you, but you have to pick one or two concrete things. You can't be like, "I don't know, what were you thinking?" He doesn't know anything about startups and you're lucky he even thought of you at all. You're going to now throw it back to him to plan out what he might do for you? No, you have to make an ask.

Second, anything you come up with is barely going to register for him in terms of level of impact, but it's going to be more then game changing for you--it's going to feel ridiculous.

Maybe your company is seed funded, or has some friends and family, or is barely more than a Powerpoint. Even if you have your Series A, the scale that you're operating on probably doesn't even come close to what he's been thinking about these days. He's on the "ending malaria/making sure every woman in the world gets equal pay" kind of level", and you're out there building an app with three devs, some cheese dip and an office dog. Even if you have a worthwhile mission, you're going to have to get over the fact that anything that he could come up with that he'd pay attention to is going to feel crazy to even ask of him.

But this is how you make a leap as a startup.

One of the easiest things you can ask of something like that is to invest. Investing insures that someone is always part of your company. It gives you an excuse to e-mail them and your updates keep you top of mind for them. It gives you an excuse to ask for more later. Getting someone to invest in your next round is like getting to wish for more wishes and having it granted.

Get over whether you know if this person invests or not or what size check they can write. Any person who gets to this level of success could probably write at least a $10k check or maybe more than you think. Remember that you're not asking for their money--you're providing them with a great opportunity for them to trade their wealth for interestingness. This is something they do all the time in a variety of ways.

Advisory boards are also a great way to rope people in that you probably have no business getting on boards. The key is to make them about something bigger than just your company. If you're a financial startup, make them about financial empowerment. If you're a fashion company, make it about style trends. If you're a consumer product, make it about world class customer experience, etc.

It's really easy to be focused on short term goals as a founder--getting to that next raise, making that next hire, or just making sure your bills are paid. The companies that make huge leaps in impact and value execute these kinds of headline making moves, leaving their competition far behind in the rear view mirror. Knowing what these moves could even be is hard, and it's probably something worth talking to your investors or thought partners about, and definitely something to plan around. This comes into play so many times. People you know will say, "Hey, I know the former CEO of X and she's retiring and looking for something to do."